Trifluoroacetic acid → (r)-2-[3-Chloro-4-(tetrahydro-furan-2-ylmethoxy)-benzyl]-morpholine

HRID 2253002Notes

Reaction equation

C(N1CC[O:11][C@H:10]([CH2:14][C:15]2C=CC=[C:17](C=CC3C=NC=CC=3)[CH:16]=2)C1)(OC(C)(C)C)=O.C([N:36]1[CH2:41][CH2:40][O:39][C@H:38]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[C:45]([Cl:50])[CH:44]=2)[CH2:37]1)(OC(C)(C)C)=O.C(O)C1OCCC1.C(O)(C(F)(F)F)=O>>[Cl:50][C:45]1[CH:44]=[C:43]([CH:48]=[CH:47][C:46]=1[O:49][CH2:17][CH:16]1[CH2:15][CH2:14][CH2:10][O:11]1)[CH2:42][C@H:38]1[O:39][CH2:40][CH2:41][NH:36][CH2:37]1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 7360Tetrahydrofurfuryl alcohol

HCID 67073025n-Boc-(r)-2-(3-chloro-4-hydroxybenzyl)morpholine

HCID 67073511N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine

Product 1

HCID 67073384(r)-2-[3-Chloro-4-(tetrahydro-furan-2-ylmethoxy)-benzyl]-morpholine

Procedure

Example 52 was prepared using the same procedure as described for example 7 starting from example 7, intermediate (a), N-BOC-(R)-2-(3-chloro-4-hydroxybenzyl)morpholine and tetrahydrofurfuryl alcohol. The resulting intermediate was deprotected with TFA as described for example 7 to yield the desired morpholine example 52 as a colorless oil (26 mg, 52% over 2 steps) after purification by HPLC.

Workup

customExample 52 was prepared

Sources & evidence

ORD record: ord-df3ea5b0fafe47c6b0e8c753a31eb690
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323466B2

Reaction notes

Loading…